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Synthesis 2005(19): 3183-3185  
DOI: 10.1055/s-2005-918460
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted α-Acetamido Acrylates Using Cheap Monodentate P-Ligands

Manfred T. Reetz*, Xiaoguang Li
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim/Ruhr, Germany
Fax: +49(208)3062985; e-Mail: reetz@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 28 September 2005
Publication Date:
14 November 2005 (online)

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Abstract

The asymmetric Rh-catalyzed hydrogenation of β,β-di­substituted α-acetamido acrylates, which are notoriously difficult substrates, is possible using readily available BINOL-derived monodentate­ phosphites or phosphonites. Essentially quantitative conversion and enantioselectivities of 95-97% ee are readily achieved, making the process industrially viable.

Key words

amino acids - asymmetric catalysis - hydrogenations - rhodium - chiral auxiliaries

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